Efficient and scalable synthesis of thiazole fused benzazepine as a D2 partial agonist

Tetrahedron Letters

Volumn 53, Issue 44, 2012, Pages 5833-5836

  Xiong, Hui ^a   Wu, Ye ^a   Lehr, Scott G ^a   Blackwell, William ^a   Steelman, Gary ^a   Hulsizer, Jim ^a   Urbanek, Rebecca A ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

Benzothiazole synthesis; D2 partial agonist; Heterocycle synthesis; Process route

Indexed keywords

ARIPIPRAZOLE; BENZAZEPINE DERIVATIVE; TETRAHYDROBENZAZEPINE; THIAZOLE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; COLUMN CHROMATOGRAPHY; CYCLIZATION; DEPROTECTION REACTION; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; NITRATION;

EID: 84866747034     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.08.035     Document Type: Article

References (30)

1. B.L. Roth, D.J. Sheffler, and W.K. Kroeze Nat. Rev. Drug Discovery 3 2004 353
2. T. Kikuchi, K. Tottori, Y. Uwahodo, T. Hirose, T. Miwa, Y. Oshiro, and S.J. Morita Pharmacol. Exp. Ther. 274 1995 329
3. Y. Oshiro, S. Sato, N. Kurahashi, T. Tanaka, T. Kikuchi, K. Tottori, Y. Uwahodo, and T. Nishi J. Med. Chem. 41 1998 658
4. M.A. Davies, D.J. Sheffler, and B.L. Roth CNS Drug Rev. 10 2004 317
5. W.A. Kinghorn, and J.P. McEvoy Expert Rev. Neurother. 5 2005 297
6. D.D. Miller, J.M. Eudicone, A. Pikalov, and E. Kim J. Clin. Psychiatry 68 2007 1901
7. F. Yocca, and A. Altar Drug Discov. Today Ther. Strateg. 3 2006 429
8. C.A. Tamminga Curr. Neuropharmacol. 3 2005 3
9. J.A. Lieberman CNS Drugs 18 2004 251
10. D.J. Wustrow Adv. in Med. Chem. 5 2000 115
11. J.H. Kehne, T.H. Andree, and J.N. Heinrich Curr. Top. Med. Chem. 1068 2008 8
12. S.M. Stahl CNS Spectr. 13 2008 279
13. R.W. Feenstra, J. de Moes, J.J. Hofma, H. Kling, W. Kuipers, S.K. Long, M.T.M. Tulp, J.A.M. van der Heyden, and C.G. Kruse Bioorg. Med. Chem. Lett. 11 2001 2345
14. D.S. Johnson, C. Choi, L.K. Fay, D.A. Favor, J.T. Repine, A.D. White, H.C. Akunne, L. Fitzgerald, K. Nicholls, B.J. Snyder, S.Z. Whetzel, L. Zhang, and K.A. Serpa Bioorg. Med. Chem. Lett. 21 2011 2621
15. Favor, D. A.; Johnson, D. S.; Repine, J. T.; White, A. D. WO 200,61,03,559, 2006.
16. Blackwell, W. C., III; Hulsizer, J.; Liu, J.; Steelman, G.; Urbanek, R.; Widzowski, D.; Wu, Y. WO 200,91,05,026, 2009.
17. Koshio, H.; Asai, N.; Takahashi, T.; Shimizu, T.; Nagai, Y.; Kawabata, K.; Thor, K. B. WO 2011111817, 2011.
18. Gribble, A. D.; Forbes, I. T.; Lightfoot, A.; Payne, A. H.; Walker, G. WO 200,30,99,792, 2003.
19. Bonanomi, G.; Damiani, F.; Gentile, G.; Hamprecht, D. W.; Micheli, F.; Tarsi, L.; Tedesco, G.; Terreni, S. WO 200,51,18,549, 2005.
20. Pooni, P.; Merchant, K. J.; Buffham, W. J. WO 201,10,83,314, 2011.
21. Pooni, P. K.; Merchant, K. J.; Buffham, W. J. WO 201,10,83,314, 2011.
22. Adam, G.; Binggeli, A.; Maerki, H.-P.; Mutel, V.; Wilhelm, M.; Wostl, W. EP 10,74,549, 2001.
23. Bhatti, B. S.; Cuthbertson, T. J.; Mazurov, A.; Mitchener, J. P., Jr.; Munoz, J. A.; Murthy, V. S.; Xiao, Y.-D.; Yohannes, D. WO 201,00,96,384, 2010.
24. Busch-Petersen, J.; Cooper, A. W. J.; Laine, D. I.; Palovich, M. R.; Davis, R. S.; Fu, W. WO 200,50,94,834, 2005.
25. Purchased from Ramidus AB.
26. I.A. Kaye, and I.M. Roberts J. Am. Chem. Soc. 73 1951 4762
27. J.L. Wood Org. React. 3 1946 240
28. I.A. Ismail, D.E. Sharp, and M.R. Chedekel J. Org. Chem. 45 1980 2245
29. K. Ulanenko, E. Falb, H.E. Gottlieb, and Y. Herzig J. Org. Chem. 71 2006 7053
30. M.E. Giles, C. Thomson, S.C. Eyley, A.J. Cole, C.J. Goodwin, P.A. Hurved, A.J.G. Morlin, S. Atkinson, C. Just, J.C. Dean, J.T. Singleton, A.J. Longton, I. Woodland, A. Teasdale, B. Gregertsen, H. Else, M.S. Athwalm, S. Tatterton, J.M. Knott, N. Thompson, and S. Smith J. Org. Proc. Res. Dev. 8 2004 628